10 Best Chick Flick Comedies

The list of the 10 best chick flick comedies includes some of the most charming and endearing movies ever made. Though generally thought to be made for and marketed to women specifically, a good chick flick can be entertaining any demographic. Relationships, head games and handsome leading men are staples of this genre.

“Th Devil Wears Prada” This movie, starring Anne Hathaway and Meryl Streep, is one of the best chick flick comedies ever. Streep plays a no-nonsense publishing executive and Hathaway, her smart but struggling assistant, is learning about the fashion industry. Streep’s performance is hilarious and steals every scene.

“Bridget Jones’s Diary” This movie is about a bumbling, stumbling and slightly plump gal who manages to get into a physical relationship with her hunky boss. As things get complicated there, she may miss out on a much better opportunity. There are plenty of bad elements in this film, but this movie is funny nonetheless.

“Philadelphia Story” Though certainly not called this at the time it was made in 1940, this movie is one of the best chick flick comedies. A legendary cast includes Cary Grant, Katharine Hepburn and Jimmy Stewart in this film about a socialite who is planning for her wedding but finds things getting complicated as the event nears.

“When Harry Met Sally” Billy Crystal inexplicably became a big star in chick flicks in the '80s and '90s and this one was perhaps the best. Starring opposite Meg Ryan, they play a couple who deal with relationship issues—with each other and others—over several decades. The fake orgasm diner scene is legendary.

“Sex and the City” This movie, based on the popular HBO show, is one of the best chick flick comedies. The femme-fantastic crew of Carrie, Miranda, Samantha and Charlotte deal with a variety of issues facing women in their '40s, primarily around the relationships in their lives.

“Four Weddings and a Funeral” This movie launched the career of gal-favorite Hugh Grant and is one of the best chick flick comedies. A group of friends get together over the course of several months at… well, four weddings and a funeral. Dry British humor makes this movie very funny.

“The Truth about Cats and Dogs” This film stars Uma Thurman and Janeane Garofalo and is one of the best chick flick comedies you’ll see. Garofalo is the host of a radio call-in show and sends an attractive friend in her place on a blind date. Both girls fall for the guy and several funny situations ensue.

“Fried Green Tomatoes” This movie was nominated for two Oscars and is one of the best chick flick comedies. A great cast is rounded out with Kathy Bates, Mary Stuart Masterson, Mary-Louise Parker and Jessica Tandy and deals with the trials and tribulations of their lives.

“Sleepless in Seattle” Tom Hanks is opposite Meg Ryan in this movie about a man who calls into a relationship-focused radio show. The heart-rendering comments he gives regarding the loss of his wife sparks a nationwide outpouring of women looking to take his wife’s place.

“My Best Friend’s Wedding” Julia Roberts is the star of this movie about a couple who in college agreed to marry each other should neither be married when they turn 28. Roberts’s character is somewhat jealous and tries to derail the nuptials from taking place.